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Adipic acid

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Name

Adipic acid

EINECS 204-673-3
CAS No. 124-04-9 Density 1.251 g/cm3
Solubility methanol: 0.1 g/mL, clear, colorless Melting Point 151-154 °C(lit.)
Formula C6H10O4 Boiling Point 338.539 °C at 760 mmHg
Molecular Weight 146.142 Flash Point 172.745 °C
Transport Information UN 9077 Appearance white crystalline powder
Safety 26 Risk Codes 36
Molecular Structure Molecular Structure of 124-04-9 (Adipic acid) Hazard Symbols IrritantXi
Synonyms

FEMA No. 2011;Adipic acid;Hexane diacid;Heptanedoic;1, 4-Butanedicarboxylic acid;Adipinsaeure;Hexan-1,6-dicarboxylate;Kyselina adipova;Inipol DS;hexanedioic acid;1,4-butanedicarboxylic acid;Adipate;Hexanedioate;Adilactetten;Molten adipic acid;Acifloctin;1,6-Hexanedioic acid;Acinetten;

 

Adipic acid Specification

The Adipic acid is an organic compound with the formula C6H10O4. The IUPAC name of this chemical is hexanedioic acid. With the CAS registry number 124-04-9, it is also named as Adipinsaure. The product's categories are Industrial/Fine Chemicals; alpha,omega-Alkanedicarboxylic Acids; alpha,omega-Bifunctional Alkanes; Monofunctional & alpha,omega-Bifunctional Alkanes. Besides, it is a white crystalline powder, which should be stored in a closed and dry place at temperature of 4 °C.

Physical properties about Adipic acid are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 1; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 4; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 5; (8)Polar Surface Area: 74.6 Å2; (9)Index of Refraction: 1.476; (10)Molar Refractivity: 32.975 cm3; (11)Molar Volume: 116.827 cm3; (12)Polarizability: 13.072×10-24cm3; (13)Surface Tension: 52.486 dyne/cm; (14)Density: 1.251 g/cm3; (15)Flash Point: 172.745 °C; (16)Enthalpy of Vaporization: 63.952 kJ/mol; (17)Boiling Point: 338.539 °C at 760 mmHg.

Preparation: currently adipic acid is produced from a mixture of cyclohexanol and cyclohexanone called "KA oil", the abbreviation of "ketone-alcohol oil." The KA oil is oxidized with nitric acid to give adipic acid, via a multistep pathway. Early in the reaction the cyclohexanol is converted to the ketone, releasing nitrous acid:
HOC6H11 + HNO3 → OC6H10 + HNO2 + H2O
Among its many reactions, the cyclohexanone is nitrosated, setting the stage for the scission of the C-C bond:
HNO2 + HNO3 → NO+NO3- + H2O
OC6H10 + NO+ → OC6H9-2-NO + H+
Side products of the method include glutaric and succinic acids.

Uses of Adipic acid: the majority of adipic acid is used as monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming 6,6-nylon. Other major applications also involve polymers: it is a monomer for production of Polyurethane and its esters are plasticizers, especially in PVC. In medicine, adipic acid has been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidic drugs. It has also been incorporated into the polymeric coating of hydrophilic monolithic systems to modulate the intragel pH, resulting in zero-order release of a hydrophilic drug. The disintegration at intestinal pH of the enteric polymer shellac has been reported to improve when adipic acid was used as a pore-forming agent without affecting release in the acidic media. Other controlled-release formulations have included adipic acid with the intention of obtaining a late-burst release profile. Small but significant amounts of adipic acid are used as a food ingredient as a flavorant and gelling aid. It is used in some calcium carbonate antacids to make them tart.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes.  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: C(CCC(=O)O)CC(=O)O
(2)InChI: InChI=1/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
(3)InChIKey: WNLRTRBMVRJNCN-UHFFFAOYAY
(4)Std. InChI: InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
(5)Std. InChIKey: WNLRTRBMVRJNCN-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 680mg/kg (680mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BLOOD: HEMORRHAGE
Journal of Agricultural and Food Chemistry. Vol. 5, Pg. 759, 1957.
mouse LD50 oral 1900mg/kg (1900mg/kg) GASTROINTESTINAL: OTHER CHANGES Journal of Agricultural and Food Chemistry. Vol. 5, Pg. 759, 1957.
rabbit LD50 oral > 11gm/kg (11000mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(9), Pg. 72, 1983.
rat LD50 intraperitoneal 275mg/kg (275mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES

BLOOD: HEMORRHAGE
Journal of Agricultural and Food Chemistry. Vol. 5, Pg. 759, 1957.
rat LD50 oral > 11gm/kg (11000mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(9), Pg. 72, 1983.

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